Resin substitute produced by friedel crafts reaction



' Patented Jaa'ie", 1926.

To-aZZ whom it may com-era:

" dispensable for the 'In the ma tlon. I

.alka-lies or acids.

cent of the total max. I

Further'beIoW some examplesot new res-Q inous bodiesand of the means ofmakingf-ATE's amen rnmmn rum mus PATENT omen.-

CHEMISOHE-I'ABBIK Aux-scrim! (vomr. n. scnnm ve), or warm, ennmmv.

I ansm surs'rrru'rs rnonucnn Be it known that we, Enron Fnmmo and HANS JonnA'N citizens of Germany, residing 'at Berlin, Germany, .have inventedcertain new anduseful Im rovementsin Resin Substitutes Produced FriedelGrafts Reac-' tion, of which the bllowing is a specifica-.

Our invention relates to resinous I .compounds for use as substitutesfor natural r'esins and the like, and to the method: of making same.

- As is well known tothose skilled in the art, if suitable compoundssuch as benzene and its'homologues or other hydrocarbons or theirderivatives are acted upon with chlorides and other compounds containingchlorineaccording to the reaction indicated-by Friedel' and Crafts;there are formed besides the products which it is intended to obtam,also varying quantities of resinous by-products. We have now discoveredthat by causing this reaction to take place under certain suitableconditions, almost all of the reaction products can be. obtained in theform of valuable viscous liquids some of which on solidifying have aresinous character. These products being produced according toFriedeLCra/rts reactlon are slightly fluorescent and incontradistinction to natural'resins will not dissolve iii nor beattacked by We have ascertained more particularl that in many cases theanhydrous metal ha ides, which uptill now were consideredincarryingoutof Friedel- Crafts reactiglnf can berepla'ced-by chemicallv inert sace cat'alyzers, :Eorinstance fullers earth," franconitc, to '1 and thelike (which are hydrossilicates (if-aluminium and magnesium). I I I'or-ity of cases, the catalytically active substance should. notexceedpersame in accordancewith ourinvention will I and sequence-of o be.given, but we' wish it to be understood that we do not intend to belimited to 'th'e exact compounds, nor tq the particular kind n -'r edii-t examples, for obvious modiqcsgiens will readily occur to apersonskilled I n the art.

Fe al --'-E r cous bodiesare .o tainedg,

-Appllcatlon fled A e as, 192:. Serial m. spasm.

' I naphthalene and'napthalene tetrachloride are intimately. mixed witha quan 'ty of fullers earth equalin about 0.1 pc i the total weight.This mixture is 'slowly heated, and at a temperature of about C. avigorous development of hydrochloric acid is started. After theprincipal reaction hasicome to an end, the viscous liquid is heated atforabout two hours. The product of reaction which has a dark green coleris now dissolved in 'a'suitable solvent, for instance carbontetrachloride, and the entof JORDAN, OF BERLIN, GEBKANY, ASSIG NORS TOTHE FIRM:

. solution is well shaken with water. Upon I removal of the solvent,there remains a dark 1 colored hard resin of valuable which can bedecolorized, if desire ropeftile:

[wit t aid-of fullers earth or the like. 'lh'e resinobtained is solublein carbon tetrachloride, I

acetone, ethyl acetate and hydrocarbons of i5 the benzene t pe', butinsoluble in alcohol. It softens at a ut 65, C. .On this resinbeenellow.

mamplc 2.-40 parts by lene tetrachloride "are boiled w 320 parts of to.an. end. ,The

to. Example 1.f The final: product is a viscous liquld. colored a darkgreen and readweight of acety'-.

.. ing bleached, its color will change to; g i

ily dissolving 1n carbon tetrachloride, chlorofor'm and hydrocarb n of.the benzene phenolic bodies ype. y w

Emamplc3i-Eqhal parts by weight of'the resent'in low temperature tar andof 'nap lithalene tetrachloride are,

:heated with. 0.1 percent .120 C. until nomore hydrochloric acid iullersearth to is developed. The product of reaction is then treated furtheras described with refer:

.ence to Example 1. "The final'product'is a dark greenmass readilysoluble in nd softening at, about 809.0.

We clainiz- .1. The method alcohol I of making substitutes for naturalresins which consists-in subjectm r-j, an aromatic compound of the kmdwh c can react with certain halogen. compounds. 1;

accerdingto Friedel "and Craits reaction, to the-{actiono'f s'uc h athalo I the. resence'ofso-much o a s' ace'cataly ser t at th formation-ofaddition products is substantially revented and 'mamly yisen' compound mI a tained.

2. The mehod of making substitutes for natural resins which consists insubjecting an aromatic compound of the kind which can react with certainhalogen compounds,

according to Friedel and Crafts reaction, to the action of such ahalogen compound In a. the presence of a quantity of a surface catarlyser not exceeding ten percent.

much of a surface catalyser that the formation of addition products issubstantially prevented and mainly viscous bodies are ob- 4. The methodof making substitutes for natural resins which consists in subjecting anaromatic compound ofthe kind which. can react with certain halogencompounds according to Friedel and Crafts reaction, to the action of themolecular quantity of such a halogen compound in the presence of a.quantity of a surface exceeding ten percent.

5. The method of making substitutes for natural resins which consists insubjecting an aromatic compound of the kind which can react with certainhalogen compounds according to Friedel and Crafts reaction, to theaction of such athalogen compound in the presence of a quantity offullers earth not exceeding ten percent.

6. As a new product, a 'res nsubstitute of dark green color showing aslight fluores cence, softening above 60 C., dissolving in carbontetrachloride, chloroform and hydrocarbons of the benzene series andresistive against the action of alkalis and acids.

In testimony whereof we atlixour signatures.

ERIGH FREUND. HANS JORDAN.

catalyser not,

